Trimethylsilyl iodide → 1-Ethyl hydrogen 4-oxo-4H-quinolizine-1,3-dicarboxylate

HRID 255599Notes

Reaction equation

HRID 255599 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17]([O:19]CC)=[O:18])[C:9](=[O:16])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2)=[O:5])[CH3:2].C[Si](I)(C)C>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:17]([OH:19])=[O:18])[C:9](=[O:16])[N:10]2[C:15]=1[CH:14]=[CH:13][CH:12]=[CH:11]2)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 262620Diethyl 4-oxo-4H-quinolizine-1,3-dicarboxylate

Product 1

HCID 6215091-Ethyl hydrogen 4-oxo-4H-quinolizine-1,3-dicarboxylateYield 87.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1,3-diethoxycarbonyl-4H-quinolizin-4-one (1 g) in chloroform (20 ml) was added trimethylsilyl iodide (0.49 ml) at room temperature and the mixture was stirred for 4 hours and heated with reflux for 4 hours. After cooling to room temperature, the mixture was washed with water, aqueous sodium thiosulfate, and brine. Drying over magnesium sulfate and evaporation gave a crystalline residue, which was washed with isopropyl alcohol to give 1-ethoxycarbonyl4H-quinolizin-4-one-3-carboxylic acid (794 mg).

Workup

  1. temperatureheated
  2. temperaturewith reflux for 4 hours
  3. washthe mixture was washed with water, aqueous sodium thiosulfate, and brine
  4. dry with materialDrying over magnesium sulfate and evaporation
  5. customgave a crystalline residue, which
  6. washwas washed with isopropyl alcohol

Sources & evidence

ORD record
ord-8ca7f7cbfe3a459bbc405f84de8111ee
Source dataset
uspto-grants-1987_10
Patent number
US04698349

Reaction notes

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